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Roland is found blocking your way to Georgy's boat. He asks why Alex, Joel and Georgy are trying to leave the island. Georgy tells Roland that this isn't his business, and Joel explains that he found what he was looking for. After Georgy and Joel speak, Roland claims that you won't listen to reason, then starts combat.

He's viewed as a pushover partly because he's timid, and partly because he takes care of Crows whom are destroying Garbage Island's food. This leads to Roland being bullied relentlessly. Georgy is Roland's biggest bully number one due to him enflaming hatred towards Roland.

Roland has the biggest cognitive dissonance over staying at Garbage Island. The more Roland suffers at Garbage Island due to the inhabitants and the stench of his living quarters, the more Roland tries to justify being on the island.

Richie, on the other hand, has a crush on Roland and believes he's doing the right thing. Roland isn't aware that Richie loves him because Richie is too scared to approach him partly because he's shy, and partly because he fears he'll be mocked for being nice to Roland.

Roland is an extremely powerful boss that servers as a gate for the rest of the game. It's heavily advised that the player saves as much Mystery Jerky and Bottles for the fight. If you've gave Augustus Estrada his Cockroach Chalk back previously and your entire party becomes KO'd at any point, Augustus will interrupt the battle and
revive your entire party, and then will scold Roland. The scolding make Roland depressed, which will significantly decrease Roland's stats.

This phase is when Roland is at his strongest. He has a whopping 2,500 hp, the second highest in the entire game (beaten only by Chaz) and has an ability that gives Ironbody, which reduces taken damage by 60%. These two factors make him a huge damage sponge. Every 5 turns, Roland will use the skill "Gear Up", which increases his ATK by 90% and forces him to use Big Swing the next turn, which hits the entire party. The one saving grace is that he occasionally becomes astounded by your stupidity, which gives you a free turn. When Roland reaches 50% hp or below, Roland loses his inhibition and timidity and stops becoming astounded by you. When he reaches 0% hp, the player is booted from battle and is treated to a small cutscene. After the cutscene ends, Phase 2 begins.

Roland has been significantly weakened by the last fight. But despite that, he still chooses to fight for what be believes in. His max HP dropped from 2,500, to 800 and he now deals average non-boss damage, and begins wasting his turns by defending himself and kicking up sand. Roland also lost the ability to use the Gear Up + Big Swing combo. Upon reaching 0% HP, he coughs up blood and begins Phase 3.

Roland is bleeding heavily and has lost all ability to deal damage to you. He now starts crying, praying and coughing up blood, while occasionally using scratch as a last ditch effort. Unfortunately, he's so weak that his scratches do no damage. When he reaches 0% HP, he begs for the Cellophane Communion to embrace him, and at long last, dies.

This strategy is based around Joel and Georgy throwing Bottles at Roland until he dies.

On the first turn of combat, have Joel use Single Out, have Georgy use Brag, and have Alex use Goat Headbutt. If you're lucky, Roland should be Stunned, Weird, Wary and also be only directing damage toward Georgy. On the second turn, have both Joel and Georgy toss bottles at him. Rinse and repeat, while pausing to defend/dodge Big Swing when Roland is Geared Up.

This strategy is based around giving Augustus back his Cockroach Chalk, and then dying intentionally.

When entering combat, play like you usually would, but refrain from using healing items and defensive skills, like Dive. Eventually, you'll die, and if you've gave the Chalk, Augustus will intervene and revive everyone. When a party member gets revived, they get the status effect "Rage" which significantly increases your Crit Chance. Roland will also be forced to Cry and will become Depressed, which will decrease Roland's DEF, ATK, AGI and HIT. The player buff along with Roland's nerfed stats makes the entire phase significantly easier.

This strategy is based on using the Gun Toss + Roll Out combo to redirect then evade all damage Roland tries to put out.

On the first turn of combat, have Joel simply use Gun Toss to obtain the Taunt status effect. Taunt increases the afflicted characters Target Rate (TGR) to 1000%, making the enemy almost always focus them. On the second turn, use Roll Out, which gives Joel Dodge. Dodge increases your physical EVA to 100%, meaning that no physical skills (Like Punch and Big Swing, Roland's most used skills) will connect with the afflicted character. If Taunt is removed from Joel by one of Roland's bottles, use Load It In (if low on SP), Gun Toss, then continue using Roll Out. If Joel starts getting low on SP, either take a break from Dodge and use Load It In, or have Georgy or Alex feed him a Diet Cocola Cola mid-Dodge.